Iron-Catalyzed C–H Alkylative Ring Openings of Oxabicyclic Alkenes

Organic Letters 2026 Open access

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Authors: Andrea Serafino, Erika Barocelli, Andrea Secchi, Cristian Pezzato, Prof. Dr. Lutz Ackermann, Stefano Santoro, Gianpiero Cera
DOI: 10.1021/acs.orglett.5c04816
Cited by: 2
References: 65

Abstract

We report the iron-catalyzed C-H alkylative ring openings of oxabicyclic alkenes by chelation assistance. The method converted a broad family of benzamides into highly functionalized dihydronaphthen-2-ol derivatives, amenable to further synthetic transformations by removing the triazole directing group. Remarkably, the iron catalysis displayed complete chemo- and regioselectivities in converting oxabicyclic alkenes functionalized at the bridgehead carbons. Mechanistic investigations, by means of DFT calculations, fully elucidated the mechanism of the iron catalysis.

Fields of Study & Subjects

Catalytic C–H Functionalization Methods Cyclopropane Reaction Mechanisms Asymmetric Hydrogenation and Catalysis

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
2
Pages
691–696
Publication date
7 January 2026
Language
EN